2-tert-butyl-1-(2-hydroxyethyl)-5-nitro-1H-indole-4-carbonitrile → 5-amino-2-tert-butyl-1-(2-hydroxyethyl)-1H-indole-4-carbonitrile

HRID 1964459Notes

Reaction equation

HRID 1964459 reaction equation
[C:1]([C:5]1[N:6]([CH2:19][CH2:20][OH:21])[C:7]2[CH:8]=[CH:9][C:10]([N+:16]([O-])=O)=[C:11]([C:14]#[N:15])[C:12]=2[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:16][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:19][CH2:20][OH:21])[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:13][C:12]=2[C:11]=1[C:14]#[N:15]

Participants

4

Reactant 1

HCID 581832442-tert-butyl-1-(2-hydroxyethyl)-5-nitro-1H-indole-4-carbonitrile

Product 1

HCID 581832225-amino-2-tert-butyl-1-(2-hydroxyethyl)-1H-indole-4-carbonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-tert-butyl-1-(2-hydroxyethyl)-5-nitro-1H-indole-4- carbonitrile (180 mg, 0.63 mmol) in ethanol (6 mL) under N2 atmosphere was added Pd—C (5% wt, 18 mg). The reaction was flushed with N2 (g) and then with H2 (g) and stirred under H2 (atm) at room temperature for 1.5 hours. The reaction was filtered over Celite and concentrated to yield the product (150 mg, 93%). ESI-MS m/z calc. 257.2, found 258.5 (M+1)+. Retention time 1.26 minutes.

Workup

  1. customThe reaction was flushed with N2 (g)
  2. filtrationThe reaction was filtered over Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f9fa86a51f184626befb979bcc6bd385
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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